Best Tiramisu Whoopie Pies

Soft and fluffy chocolate espresso cookies, sandwiched with a rich mascarpone kahlua frosting, these are the perfect way to enjoy classic tiramisu flavors!

All the great flavors of tiramisu, in a fun whoopie pie sandwich cookie!

I’ve been thinking about desserts lately, especially since it’s Girl Scout cookie season (aka the best time of the year right?!).  I don’t have any copycat GS cookies, yet, but it got me thinking about other cookies that I love, like these pumpkin whoopie pies.  Since pumpkin isn’t easy to come by this time of year, I moved on to another classic flavor, tiramisu!

WHAT IS A WHOOPIE PIE?

Whoopie pies are a classic New England treat, comprised of two soft cookies (almost like cakes) with a creamy filling.  In the traditional recipe, the cookie/cakes are chocolate, and the filling is made of buttercream and marshmallow fluff.  This version uses an espresso chocolate cookie/cake and a mascarpone frosting laced with kahlua and a bit of espresso.

SO IS A WHOOPIE PIE A COOKIE OR CAKE?

That’s up for debate lol.  In my opinion they’re cookies, since the chocolate rounds are baked on a baking sheet and not in a pan like a traditional cake.  But these cookies are so soft, they taste just like cake, with a slightly crispy outside edge that is just delectable.

HOW TO MAKE TIRAMISU WHOOPIE PIES:

The process is pretty simple.  Once you make the chocolate espresso batter, bake them until the edges are set.  Let the cookies cool, then make the mascarpone frosting.  Spread frosting on one of the cookies, top with another, dust with powdered sugar, then nom nom nom!

CAN YOU MAKE WHOOPIE PIES AHEAD OF TIME?

Absolutely!  Assembled whoopie pies can be kept fresh in an airtight container (I like to refrigerate them), for 3-5 days.  The chocolate cookies can be made the day before, then sandwiched with the frosting the day of serving.  Alternatively, the chocolate cookies can be frozen for 1-2 months.

PRO TIPS FOR MAKING TIRAMISU WHOOPIE PIES:

1. When scooping the chocolate cookies, they’ll look too small, but don’t worry, they spread a little in the oven to be the perfect 2-3 bite size.
2. Use a cookie scoop for the most perfect round cookies.  The batter is really sticky, so trying to spoon the batter into a round ball is going to be really difficult.
3. Use mascarpone cheese if you can find it.  My local grocery stores carry it, usually in the “gourmet cheese” area of the store up front, not with the cream cheese.  If you can’t find it, cream cheese is an acceptable substitute.
4. You can use a piping bag and tip to pipe on the frosting if you want to be precise and fancy, or just smear some on with an offset spatula (what I usually do).
5. Dust them with powdered sugar right before serving.  If you dust them ahead of time, the sugar will absorb into the cookie and the tops will be slightly gummy in texture.

OTHER GREAT DESSERTS:

• Spiced Pumpkin Whoopie Pies
• Peanut Butter Blossoms Cookies
• Red Velvet Brownies
• Brownie-Bottom Cookie Dough Cheesecake

SHOP THE RECIPE:

• Stand Mixer – I love using my stand mixer so I can do other things while batter is mixing.
• Espresso Powder – this is the brand I used, but I found it at my grocery store.
• Cookie Scoop – perfect for these whoopie pies, but also mini-meatballs, mini cupcakes and more!
• Parchment Sheets – never struggle with curling parchment edges again!
• Baking Sheet – my favorite brand.. I’ve had them for years and they still look like new.
• Offset Spatula – perfect for spreading frostings of all kinds.

Did you make this? Be sure to leave a review below and tag me @the_chunky_chef on Facebook and Instagram!

Best Tiramisu Whoopie Pies

5 from 8 votes

Prep Time: 10 minutes

Cook Time: 12 minutes

Total Time: 22 minutes

Calories: 308

Servings: 12 sandwiches

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Soft and fluffy chocolate espresso cookies, sandwiched with a rich mascarpone kahlua frosting!

Ingredients

COOKIES

• ▢ 1 1/2 cups all-purpose flour
• ▢ 1/4 cup unsweetened cocoa powder
• ▢ 1/2 tsp baking powder
• ▢ 1/4 tsp baking soda
• ▢ 1/4 tsp kosher salt
• ▢ 1/3 cup milk (I like to use whole)
• ▢ 1 Tbsp instant espresso powder
• ▢ 1/2 tsp vanilla extract
• ▢ 6 Tbsp unsalted butter, softened to room temperature
• ▢ 3/4 cup granulated sugar
• ▢ 1 large egg

FROSTING

• ▢ 8 oz mascarpone cheese, at room temperature
• ▢ 4 oz cream cheese, at room temperature
• ▢ 1/3-1/2 cup powdered sugar (plus more for dusting if desired)
• ▢ 1/2 tsp vanilla extract
• ▢ 1 Tbsp Kahlua liqueur
• ▢ 1 tsp instant espresso powder

Instructions

MAKE THE COOKIES

• Adjust oven racks to the upper and lower thirds of the oven, and preheat oven to 350 F degrees.  Line two baking sheets with parchment paper and set aside.
• In a small mixing bowl, add flour, cocoa powder, baking powder, baking soda, and salt.  Whisk together and set aside.  To another small bowl, add milk, espresso powder and vanilla and stir together until espresso powder dissolves.  Set aside.
• To the bowl of a stand mixer, add butter and sugar and beat until creamy and fluffy, about 1 minute.  Add egg and beat until mixed in.  
• Add half of the flour mixture and mix until just combined.  Add all the milk mixture, mix until combined.  Add remaining flour mixture and mix until just combined.  Increase speed slightly and mix until smooth, about 30 seconds to 1 minute.
• Scoop batter onto prepared cookie sheets, about 2 inches apart.  Bake, rotating pans halfway through, 12-14 minutes, until edges are set and the tops spring back slightly when touched.  Cool on pans 3-5 minutes, then transfer to cooling racks to cool completely.

MAKE THE FROSTING

• Add mascarpone, cream cheese, powdered sugar and vanilla extract to the bowl of a stand mixer and beat until light and fluffy, about 1 minute.
• Add Kahlua and espresso powder to a small bowl and stir until dissolved.  Add liquid to frosting in stand mixer and beat until combined.
• If frosting is too thin, more powdered sugar can be added, or frosting can be refrigerated about an hour to firm up.

ASSEMBLE WHOOPIE PIES

• Spread frosting onto one cookie, then top with another cookie.  Repeat for all cookies.  Right before serving, dust with powdered sugar if desired.

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Nutrition Disclaimer

The Chunky Chef is not a dietician or nutritionist, and any nutritional information shared is an estimate. If calorie count and other nutritional values are important to you, we recommend running the ingredients through whichever online nutritional calculator you prefer. Calories can vary quite a bit depending on which brands were used.

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